About Our Company

In the Summer of 2002, Arkansas-bred traveler Jeremy L set down roots in Chicago, IL to carry on his father’s tradition of high-quality tours by starting Chicago’s #1 tour company.

Bobby’s Bike Hike Chicago Tour Company

Jeremy spent most of his twenties roaming Europe and became enchanted by bicycle exploration. Twenty-seven and strapped for cash, he opened Bobby’s Bike Hike, intent on inspiring Chicago visitors with the environmental & cultural benefits of bicycle tourism.





The company is named for Jeremy’s late father, Bob, a professional bus tour operator, who instilled in his son a love of education through travel, giving back to the community, health for the Earth and body, and the offering of unmatched service.

These core values became the driving tenets of Bobby’s Bike Hike.


Bobby’s began by offering unique neighborhood bicycle tours, taking visitors off the beaten path and showing off the beautiful communities of Chicago.


Bobby’s added food stops to select bicycle tours, allowing guests to experience Chicago with all five senses.


Bobby’s Bike Hike launched food-sampling walking tours. Today, Bobby’s Bike Hike takes pride in offering world-class tours that balance education, safety, and unadulterated fun.


We offer a diverse array of guided biking tours, walking tours, food tours and craft beer crawls daily. The Bobby’s team of expert guides is excited to make your visit to Chicago an unforgettable adventure.

Why Take a Guided Chicago Tour?

Good question! Did you know that the Second City is actually first when it comes to bike riding? Chicago consistently ranks at the top for both walking and biking because it’s flat and easy to access (take that NYC!). Plus, all the neighborhoods, parks, and attractions are connected through a network of sidewalks and trails. So it makes sense that the best way to experience life in Chicago is on two wheels (or two feet) alongside fun folks just like yourself.

And while it’s true that anyone can whizz from place to place in a car, bus, or boat, you miss out on soooo much. With a Chicago bike tour or a Chicago walking tour, or even renting a bike, you can actually hear the roar of Buckingham Fountain, touch the iconic lion statues at the Art Institute, and smell the Chicago-style pizza wafting through the air. Join us for a memorable Chicago tour – whether it’s a walking, bike, or food tour!

But if you do take a guided tour of Chicago, make sure it’s at the beginning of your trip. It’ll really help you become more familiar with the city’s layout and sites. You can navigate the rest of your visit more easily when you understand Chicago’s street plan. Plus, you can circle back to some of the locations or restaurants you want to visit again. We’ve found our tours make a fantastic jumping off point for discovering things to do in Chicago.

Why choose Bobby’s Bike Hike?

Founded in 2002, we were one of the first guided bike touring companies in the country and we consistently rank as the #1 sightseeing tour on Tripadvisor. Why? We’ve combined our knowledge as a second-generation tour operator with our drive and passion for tourism and travel, to create one-of-a-kind Chicago bike tours, Chicago food tours, and Chicago walking tours that speak to a variety of ages, interests, and skill levels.

Plus, our tour guides are some of the most experienced in the business. Tired of listening to a monotone voice drone on and on? Of course you are.

That’s why we take extra care to find guides that are personable, knowledgeable and most importantly, FUN.

In addition, our guides take your safety very seriously. They know the sidewalks and pathways inside and out so you’ll always be on the best route. And don’t forget, because Chicago is very flat and well connected geographically, it’s easy for everyone to zip from the Lakefront Trail to neighborhoods to Chicago’s tourist attractions.

We Have Earned Accolades From Top Tour Industry Names

We have the best tours around Chicago you will find, but don’t just take our word for it. Listen to the many people who have gone on our food tours, guided bike tours and city walking tours before. They have voted us:

  • The most organized tour company, according to the Chicago Reader
  • The best city tour, according to CitySearch
  • Award of Distinction, from Viator

You develop a good reputation like ours by giving people the experience they want, and that’s what you get at Bobby’s Bike Hike. We have even earned notice from Midwest Living, National Geographic and American Airlines magazines, all discerning publications that have written about our tours.

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